US10533129B2 - Organic electroluminescent device - Google Patents

Organic electroluminescent device Download PDF

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US10533129B2
US10533129B2 US15/557,093 US201515557093A US10533129B2 US 10533129 B2 US10533129 B2 US 10533129B2 US 201515557093 A US201515557093 A US 201515557093A US 10533129 B2 US10533129 B2 US 10533129B2
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transport layer
compound
formula
oled according
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US20180171218A1 (en
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Kam-Hung LOW
Zhe Li
Jinxin Chen
Lifei Cai
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Beijing Aglaia Technology Development Co Ltd
Guangdong Aglaia Optoelectronic Materials Co Ltd
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Beijing Aglaia Technology Development Co Ltd
Guangdong Aglaia Optoelectronic Materials Co Ltd
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Assigned to BEIJING AGLAIA TECHNOLOGY DEVELOPMENT CO., LTD., GUANGDONG AGLAIA OPTOELECTRONIC MATERIALS CO., LTD. reassignment BEIJING AGLAIA TECHNOLOGY DEVELOPMENT CO., LTD. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: CAI, LIFEI, CHEN, Jinxin, LI, ZHE, LOW, Kam-Hung
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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • H01L27/3209—
    • H01L51/5012—
    • H01L51/5056—
    • H01L51/5072—
    • H01L51/5203—
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • H10K50/15—Hole transporting layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • H10K50/16—Electron transporting layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/17—Carrier injection layers
    • H10K50/171—Electron injection layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/80—Constructional details
    • H10K50/805—Electrodes
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K59/00—Integrated devices, or assemblies of multiple devices, comprising at least one organic light-emitting element covered by group H10K50/00
    • H10K59/30—Devices specially adapted for multicolour light emission
    • H10K59/32—Stacked devices having two or more layers, each emitting at different wavelengths
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K71/00—Manufacture or treatment specially adapted for the organic devices covered by this subclass
    • H10K71/10—Deposition of organic active material
    • H10K71/12—Deposition of organic active material using liquid deposition, e.g. spin coating
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1011—Condensed systems

Definitions

  • This invention relates to a new type of organic non-doped blue light emitting devices made by organic electronic materials. It belongs to the Organic Light-emitting Device (OLED) display material field.
  • OLED Organic Light-emitting Device
  • OLED as a new type of display technology, has unique advantages such as self-illumination, wide viewing angle, low power consumption, high efficiency, thin, rich colors, fast response, extensive application temperature, low drive voltage, used to make flexible, bendable and transparent display panel and environmental friendliness, etc. Therefore, OLED technology can be applied to flat panel displays and new generation of lighting, or can be used as backlight of LCD.
  • OLED is a device made through spin-coating or depositing a layer of organic material between two metal electrodes.
  • a classic three-layer OLED comprises a hole transport layer, a light emitting layer and an electron transport layer.
  • the holes generating from the anode through the hole transport layer and the electrons generating from the cathode through the electron transport layer combine to form excitons in the light emitting layer, emitting light.
  • the OLED can emit red light, green light and blue light. Therefore, stable, efficient organic light-emitting materials with pure colors play an important role in the application and promotion of OLEDs. Meanwhile, it is also very urgent for the application and promotion of large area of panel display in OLEDs.
  • red and green light materials have made great development, which also meet the market demands of the panels.
  • blue light materials There are a series of commercially available materials for the blue light materials, and distyryl-biphenyl (DPVBi) compounds produced by Idemitsu are widely used in the early period.
  • the devices made by this type of compound have high efficiency, but these materials often have poor stability, and even worse, this type of compound often emits sky blue light, and often y>0.15 of the CIE value. Therefore, its poor stability and impure color greatly restrict the application of this type of compounds in the full-color display devices.
  • Another type of blue-light material is the Kodak ADN and tetra-butyl perylene, but their luminous efficiency is relatively poor, thus, it cannot be widely used.
  • the present invention provides an organic non-doped blue light emitting device with high luminous efficiency, excellent color purity and long lifetime.
  • An OLED comprises an anode, a cathode, and an organic layer, the organic layer at least contains one or more layer containing light emitting layer from the hole injection layer, hole transport layer, electron injection layer, electron transport layer, light emitting layer;
  • the light emitting layer is composed of a single compound with the structure of formula (I),
  • R 1 -R 17 independently represent hydrogen, deuterium, halogen, cyano, nitro, C1-C8 alkyl, C1-C8 alkoxy, C6-C30 substituted or unsubstituted aryls, C3-C30 substituted or unsubstituted aryls containing one or more heteroatoms, C2-C8 substituted or unsubstituted alkenyl, C2-C8 substituted or unsubstituted alkynyl, wherein Ar 1 -Ar 3 independently represent C6-C60 substituted or unsubstituted aryl, C3-C60 substituted or unsubstituted heteroaryl containing one or more heteroatoms, triaryl (C6-C30) amine.
  • R 1 -R 17 independently represent hydrogen, halogen, cyano, nitro, C1-C8 alkyl, C1-C8 alkoxy, C2-C8 substituted or unsubstituted alkenyl, C2-C8 substituted or an unsubstituted alkynyl, C1-C4 alkyl substituted or unsubstituted phenyl, C1-C4 alkyl substituted or unsubstituted naphthyl, or combined C1-C4 alkyl substituted or unsubstituted fluorenyl;
  • Ar 1 -Ar 3 independently represent C1-C4 alkyl or C6-C30 aryl-substituted phenyl, C1-C4 alkyl or C6-C30 aryl-substituted naphthyl, phenyl, naphthyl, pyridyl, N—C6-C30 aryl or C1-C4 alky
  • R 1 -R 2 independently and preferably represent hydrogen, halogen, C1-C4 alkyl, C1-C4 alkyl substituted or unsubstituted phenyl, C1-C4 alkyl substituted or unsubstituted naphthyl, or combined C1-C4 alkyl-substituted or unsubstituted fluorenyl; wherein R 3 -R 17 may independently represent hydrogen, halogen, C1-C4 alkyl, C1-C4 alkyl substituted or unsubstituted phenyl, C1-C4 alkyl-substituted or unsubstituted naphthyl, preferably Ar 1 -Ar 3 independently represent phenyl, tolyl, xylyl, t-butylphenyl, naphthyl, pyridyl, methyl naphthalene, biphenyl, diphenylphenyl, naphth
  • R 3 -R 17 preferably represents hydrogen
  • R1 and R2 may independently represent hydrogen, methyl, ethyl, propyl, isopropyl, t-butyl, phenyl, biphenyl, naphthyl, or combined fluorenyl
  • Ar 1 -Ar 3 may independently represent phenyl, pyridyl, tolyl, xylyl, naphthyl, methylnaphthalene, biphenyl, diphenylphenyl, naphthylphenyl, diphenylbiphenyl, (9,9-dialkyl) fluorenyl, (9,9-dimethyl-substituted or unsubstituted phenyl) fluorenyl, 9,9-spirofluorenyl.
  • R 3 -R 17 represent hydrogen preferably; R 1 , R 2 independently represent hydrogen, methyl or combined fluorenyl; Ar 1 , Ar 2 , Ar 3 independently represent phenyl and naphthyl.
  • the compounds with formula (I) have following structures
  • the said organic layers are one or more layers from hole injection layer, hole transport layer, light emitting layer, electron injection layer, electron transport layer, and in particular, not all organic layers are necessary according to the demands.
  • the said hole transport layer, electron transport layer and/or light emitting layer contain the said compound with the structural formula (I).
  • the compound with the structural formula (I) is located in the light emitting layer.
  • the OLED in the invention contains a light emitting layer, and the light emitting zone of the light emitting layer is 440-490 nm.
  • the light emitting layer is a non-doped system.
  • the total thickness of the organic layer of electronic device in the present invention is 1-1000 nm, preferably 1-500 nm, more preferably 50-300 nm.
  • the organic layer can form a thin film by vacuum coating or spin-coating.
  • the materials of the hole transport layer and hole injection layer in the present invention should have good hole transport performance, which can effectively transport the holes from the anode to the organic light emitting layer.
  • it further includes small molecule and polymer organic materials, including but not limited to tri-aromatic amine compounds, benzidine compounds, thiazole compounds, oxazole compounds, imidazole compounds, fluorene compound, phthalocyanine compounds, hexanitrile hexaazatriphenylene, 2,3,5,6-tetrafluoro-7,7′,8,8′-tetracyanoanthraquinodimethane dimethyl-p-benzoquinone (F4-TCNQ), polyvinyl carbazole, polythiophene, polyethylene, polyethylene sulfonic acid.
  • the organic light emitting layer in the present invention adopts the compounds with the structural formula (I), without doped with other materials.
  • the organic electron transport material of the organic electronic devices in the present invention should have good electron-transport performance, which can efficiently transfer electrons from the cathode to the light emitting layer.
  • These materials can select the following compounds, but not limited to oxa oxazole, thiazoles, triazole compounds, tri-diazoxide compounds, tri-aza benzene compounds, quinoxaline compounds, dinitrogen anthracene compounds, silicon-containing heterocyclic compounds, quinoline compounds, phenanthroline compounds, metal chelates, fluoro-substituted benzene compounds, in addition to the compounds in the present invention.
  • the electron injection layer can be added to the organic electronic device of the present invention as required.
  • the electron injection layer may effectively inject the electrons from the cathode into the organic layer, which is mainly selected from alkali metals or alkali metal compounds, or selected from alkaline earth metals or alkaline earth metal compounds, including but not limited to the following: lithium, lithium fluoride, lithium oxide, lithium nitride, 8-hydroxyquinoline lithium, cesium, cesium carbonate, 8-hydroxyquinoline cesium, calcium, calcium fluoride, calcium oxide, magnesium, magnesium fluoride, magnesium carbonate, magnesium oxide, in addition to the compounds in the present invention.
  • FIG. 1 is a structural charge of the device, of which, 10 denotes a glass substrate, 20 denotes an anode, 30 denotes hole injection layer, 40 denotes hole transport layer, 50 denotes light emitting layer, 60 denotes electron transport layer, 70 denotes electron injection layer, 80 denotes cathode.
  • FIG. 2 is the 1H NMR diagram of compound 89.
  • FIG. 3 is the 13 C NMR diagram of compound 89.
  • FIG. 4 is a high performance liquid chromatogram of compound 89.
  • FIG. 5 is the TGA map of compound 89.
  • FIG. 6 shows the voltage-current density curves of Embodiments 4 and 5 and Comparative Example 1.
  • FIG. 7 shows the brightness-CIEy plot of Embodiments 4 and 5 and Comparative Example 1.
  • FIG. 8 shows the light-emitting spectra of Embodiments 4 and 5 and Comparative Example 1.
  • FIG. 9 shows the current density-current efficiency curves of Embodiments 4 and 5 and Comparative Example 1.
  • the hydrogen spectra and carbon spectra of compound 89 are completely consistent with the structures.
  • the product made by the synthesis method in the invention has high purity.
  • the thermal gravametric analysis of compound 89 in FIG. 5 the decomposition temperature of this type of compound is higher than 400 degrees centigrade, indicating that it has very high thermal stability.
  • the ITO transparent conductive glass substrate 10 (with anode 20 above) is washed with detergent solution and deionized water, ethanol, acetone, deionized water in sequence, then treated with oxygen plasma for 30 seconds.
  • the voltage of the device made in 20 mA/cm2 of operating current density is 3.58 V, the current efficiency is 3.21 cd/A.
  • the CIEy at the luminance of 1000 cd/m2 is 0.0853. It emits blue light.
  • the voltage of the device made in 20 mA/cm 2 of operating current density is 3.84 V, the current efficiency is 2.83 cd/A.
  • the CIEy at the luminance of 1000 cd/m2 is 0.0888. It emits blue light.
  • OLED is made using the following compound TAT instead of compound 3, for comparison.
  • the voltage of the device made in 20 mA/cm 2 of operating current density is 4.00 V, the current efficiency is 2.46 cd/A.
  • the CIEy at the luminance of 1000 cd/m2 is 0.0952. It emits blue light.
  • the embodiments 4 and 5 are the specific applications of the material in the present invention.
  • the blue light-emitting, efficiency and luminance of the devices are higher than those in the comparison example. Therefore, as stated above, the material in the present invention has high stability, and the OLED made in the invention has high efficiency and light purity.

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  • Physics & Mathematics (AREA)
  • Chemical & Material Sciences (AREA)
  • Optics & Photonics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Organic Chemistry (AREA)
  • Manufacturing & Machinery (AREA)
  • Electroluminescent Light Sources (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
US15/557,093 2015-03-09 2015-09-01 Organic electroluminescent device Active 2036-02-17 US10533129B2 (en)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
CN201510102483 2015-03-09
CN201510102483.0A CN106033798B (zh) 2015-03-09 2015-03-09 有机电致发光器件
CN201510102483.0 2015-03-09
PCT/CN2015/088710 WO2016141692A1 (zh) 2015-03-09 2015-09-01 有机电致发光器件

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US10533129B2 true US10533129B2 (en) 2020-01-14

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US (1) US10533129B2 (ja)
JP (1) JP6581664B2 (ja)
KR (1) KR20170118785A (ja)
CN (1) CN106033798B (ja)
DE (1) DE112015006273B4 (ja)
TW (1) TWI561499B (ja)
WO (1) WO2016141692A1 (ja)

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CN108269947A (zh) * 2016-12-30 2018-07-10 广东阿格蕾雅光电材料有限公司 有机发光二极管器件
CN108299389A (zh) * 2017-12-26 2018-07-20 上海道亦化工科技有限公司 一种基于菲和咔唑的化合物及其用途和有机电致发光器件
KR102518416B1 (ko) * 2018-07-31 2023-04-06 삼성디스플레이 주식회사 저굴절층 및 이를 포함하는 전자 장치
CN111320636B (zh) * 2018-12-17 2022-09-02 广东阿格蕾雅光电材料有限公司 一种有机电致发光材料及其应用

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Publication number Publication date
DE112015006273T5 (de) 2018-01-18
DE112015006273B4 (de) 2022-02-10
WO2016141692A1 (zh) 2016-09-15
CN106033798B (zh) 2017-11-14
KR20170118785A (ko) 2017-10-25
JP2018514080A (ja) 2018-05-31
CN106033798A (zh) 2016-10-19
TW201632487A (zh) 2016-09-16
JP6581664B2 (ja) 2019-09-25
US20180171218A1 (en) 2018-06-21
TWI561499B (en) 2016-12-11

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